The prospect of satisfying a lady’s anal cravings leaves our sexual explorer needing medical attention…


This month I have to confess to a highly regrettable incident involving anal sex and stilton cheese. But first, I want to talk about having a heart attack. It started with chest pains. There was nothing new there. In fact I get them about once a week, usually when I’m enraged with my computer for not working properly. But this time I was being held in one of those automated telephone queues, listening to a female voice tell me to “press one for customer service, press two for sales, press three for technical support…” We all know this voice: it has a veneer of warmth on the surface but you can feel the ice-cold indifference lurking underneath. In the future, governments will use it to torture people.

After making my choice, I was shunted through to another list of options. Finally, after 17 minutes of listening to a ringtone, the voice came back and said, “Sorry, all our agents are busy. Please call back later.” Then the line went dead. I erupted, emitting a stream of language so depraved that a polite magazine like FHM would need to buy a year’s supply of asterisks, skulls, dollar signs and poison bottles to censor it if I wrote it down. Probably the only printable sentence was, “You fucking robot BITCH!” At the peak of my frenzy, I slammed the phone onto my desk, stood up and felt a sudden stab in my heart. This was no twinge. Instead it was as though a red hot dagger had been jammed through my ribcage by an assassin. The breath caught in my throat.

I lost all sensation in my limbs and slumped forwards onto my desk. Oddly, the only thing I could think about once the first rush of fear had pulsed through me was that I was about to die in a very stupid way. Okay, it might not be on a par with Rod Hull falling off his roof, but there was something undeniably absurd about being killed by TalkTalk. Luckily, God had other plans and slowly I began to breathe again, sucking down the air in shallow gulps.

At the hospital, they told me the attack was caused by panic rather than clogged arteries, but just to make sure I booked a full medical with BUPA. And so, a couple of weeks and £830 later, I found myself in a clinic off Harley Street. My blood, sight, hearing, cholesterol and reflexes were all tested, and found to be in excellent fettle. I was just starting to cheer up about life when one of the doctors asked me to go behind a curtain and take off my trousers. It was time for the prostate exam.

His fingers, I noticed, were long and slender. He could have been a concert pianist. What a waste. I lay on the bed with my knees hunched up, peering nervously over my shoulder as he squeezed some lubricant onto his rubber glove. He was about to penetrate me, but I felt sorry for him. He had probably grown up wanting to be a doctor, being admired for saving people in accidents and delivering babies, but then somewhere along the line he’d made the insane decision to become a proctologist. Maybe the money was good, but still. Think about it. Put on your white coat for 15 appointments a day. Fifteen rectums. Some of them diseased. Seventy-five a week. Around 4,000 a year. Every year until you retire. The smell. The bad wiping. Knowing nobody wants to shake your hand…

He inserted his index finger. It was only just inside me, up to the first knuckle, but to the virgin nerve ends of my fundament it felt as painful as the full insertion of a cricket bat handle. “Now you push back,” he said. Push back? It was all very well being molested in the name of science, but was he seriously expecting me to join in? For god’s sake, I wanted to say, just ease it up there yourself. But I’m useless at arguing with people in positions of responsibility so – very gingerly – I reversed my arse in the direction of his wrist. “That’s good,” he said soothingly. “Now push again.”

That’s good? Was he looking for a patient or a cellmate? I sighed and moved downwards, feeling his digit slide along the corrugated walls of my rectum, like a burrowing worm. Then he finally reached the gland he’d been looking for, and started to stroke it. At this point, my anal life flashed before my eyes. And I thought, why me? Because, uniquely among my circle of friends, I have never been interested in sodomy. To me, a lady’s arse is a taboo zone. Area 51. I have no wish to go there. When people ask me why, I say that the pussy and the mouth are such wonderful apertures, why would I need an alternative? But they pour scorn on this. “You must secretly fear that you’re gay,” they say.

But I know that’s not true beacuse I’ve tried a sexual encounter with a man and found it not shocking, simply not to my taste. Perhaps it all goes back to my one attempt at buggering a woman. I was stepping out with a girl called Melanie. We had met at a friend’s wedding and embarked on a vigorous sexual relationship. Like Groundhog Day, it followed the same pattern every time we met. She’d let me in the front door, we’d start kissing in the hallway, then we’d be pulling each other’s clothes off before we even got to the sofa in the front room.

There were few frills to our love-making but it was hearty and enjoyable. Like those old adverts for Skegness used to say, “So bracing.” I particularly liked the way she asked for what she wanted. Other girls might be too bashful to communicate their precise desires in the throes of passion, but not Melanie. With breathy candour, she’d say, “Turn me round” or “Do it harder” or “On my tits”. I was happy to obey. However, during our fourth or fifth grappling, she casually added another request. As we switched out of cowgirl and into the canine position, she asked me to screw her up the arse. I explained that I wasn’t into it – eliciting the response, “But I thought all boys were!” – and hoped to hear nothing more of the matter. But no.

Whenever I went round after that, she’d start pleading with me. She loved it, she said. It was amazing. She was sure I’d love it too if I gave it a chance. I gave these arguments the stone wall treatment easily enough, and I reckoned she was on the brink of giving up. But then, as we lay one afternoon in a post-coital hug, she mentioned that anal sex made her feel “fuller”. This hit a nerve. I am plagued by severe cock size anxieties, and became immediately paranoid that I wasn’t big enough to satisfy her with normal sex. That was it! Her strange insistence on sodomy… it was because she couldn’t even feel me inside her vagina! I could well believe it. Oh god. Oh god.

There was only one thing to do. The next time we met, I assured her, she would be treated to the love that dare not speak its name. Except in Parkhurst. When the day came, I paced around at home like a condemned man. From my pals, I’d heard nightmare tales of foul odours and nasty little accidents. I could see the future coming towards me with slow inevitability, like a goods train winding down the track. I was going to pull my penis out of her and see it smeared with excrement. It would go in as pink as bubblegum and come out looking like a slightly melted Crunchie.

Mind you, if it was going to be an awful evening, I figured I should at least try to save some money. Usually, I shelled out for a pizza delivery after our romps, but tonight she would have to fend for herself. I was going to have a nice, cheap, filling meal before getting a cab to her place. Sadly, at the time I was living with two other bachelors, and everyone’s food was fair game. If you didn’t actually keep it stored in your cheeks like a hamster, there was no guarantee it would be there in the morning. So instead of finding the curry meal I’d bought at Waitrose, I was greeted by a fridge containing only a loaf of bread and a lump of stilton. I recognised the cheese. It had been dwelling on the top shelf for several weeks. But was it still edible? If it had been cheddar or brie I could have told in an instant because it would be covered with mould. But stilton, of course, was already mouldy. It might be fresh, it might date from the ’50s – without carbon dating there was no real way of telling.

But it was a night for taking chances, so I decided to toast it on a slice of Hovis, figuring that the heat would kill off any germs. Once I’d finished it, I brushed my teeth and called a taxi. Outside her front door, I hesitated before knocking. This was it. Thirty-two years old. Time to drop the ‘A’ bomb. True to form, we were kissing within moments. She was giggly and excited about what was to come, joking about taking my virginity and promising to be gentle. To soften me up for the ordeal ahead, she lay me down and gave me a glorious 69 blow-job, sousing my cock with warm saliva. But something was wrong. I could feel my stomach convulsing, as though an angry cobra had woken up inside it. My forehead went clammy. “Mel,” I said, pushing at her hips. “I think I’m feeling sick.” She looked at me over her shoulder with narrow eyes, suspecting that I was trying to shirk my duty. Another wrenching motion went through my gut and I felt that unmistakable feeling, the one that tells you that you have about three seconds to get to a lavatory before you explode.

Mel was still sitting astride me, so I needed to buck her off before I could make it to the bathroom. Unfortunately, all that love-making had given her strong thighs and a good sense of balance, so she managed to stay aboard. “If you’re doing this to get out of…” she began, but she never finished the sentence. A watery blast of faeces pulsed out of me in a sudden jet, as though somebody had filled a hot water bottle with sewage and then stabbed it with a steak knife. She screamed. I groaned. Waves of diarrhoea followed. Two hours later, I was wrapped in an old blanket and shivering like a sick dog. Mel was downstairs washing her sheets for the second time. To be fair, she was quite kind about the whole thing once she saw how ill I was, but clearly the relationship was doomed. And with it, my intent to have anal sex with anyone.

Mind you, after the expense of that BUPA check up, I may change my mind. As I left the clinic, feeling hollowed out and traumatised, I started thinking how it was all TalkTalk’s fault. I’d waited months for them to connect my broadband, then months more for them to compensate me when it failed. I must have spent 20 hours on the phone but I never got a penny back. They were the cause of my panic attack, and thus directly to blame for the brutal molestation of my arse. Vengeance will be mine. I will track down Charles Dunstone, the flabby billionaire who owns the company. I’ll creep into his mansion one night, pull down his silk pyjamas, and give him what Melanie wanted all those years ago. But in this case, like rape, it won’t be about sex. Oh no, Charles. This will be a crime of violence.